O-Phenylenediamine → Dipyridophenazine

HRID 537590Notes

Reaction equation

HRID 537590 reaction equation
[N:1]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][N:12]=3)[C:7](=O)[C:6](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:17]1([NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:23]>C(O)C>[CH:4]1[C:5]2[C:6]3[C:7]([C:8]4[CH:9]=[CH:10][CH:11]=[N:12][C:13]=4[C:14]=2[N:1]=[CH:2][CH:3]=1)=[N:24][C:17]1[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=1)[N:23]=3

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 728101,10-Phenanthroline-5,6-dione

Product 1

HCID 3081616DipyridophenazineYield 55.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Into a 200 mL recovery flask were placed 1,10-phenanthroline-5,6-dione (1.09 g, 5.19 mmol) and ethanol (10 mL), and the mixture was stirred to provide a suspension. And then, 1,2-phenylenediamine (0.592 g, 5.20 mmol) and ethanol (40 mL) were added to the suspension, and the mixture was refluxed for 2 hours. After allowing the reaction liquid to stand overnight, an insoluble substance was collected by filtration, and washed with cold ethanol. And then, the product was recrystallized with ethanol, and dipyrido[3,2-a:2′,3′-c]phenazine (Qxphen) (0.808 g) was obtained.

Workup

  1. customInto a 200 mL recovery flask were placed
  2. customto provide a suspension
  3. temperaturethe mixture was refluxed for 2 hours
  4. customthe reaction liquid
  5. filtrationan insoluble substance was collected by filtration
  6. washwashed with cold ethanol
  7. customAnd then, the product was recrystallized with ethanol

Sources & evidence

ORD record
ord-f5321428c8204688b162573a415d0ebb
Source dataset
uspto-grants-2014_10
Patent number
US08859894B2

Reaction notes

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